Potassium Iodide → 8-cyano-2-isopropoxy-11-oxo-11H-pyrido[2,1-b]quinazoline

HRID 1702612Notes

Reaction equation

HRID 1702612 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[C:9]([C:10]([OH:12])=O)[C:8]([NH2:14])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][N:17]=1.[I-].[K+].COCCOCCOCCOC>>[C:22]([C:19]1[CH:20]=[CH:21][C:16]2[N:17]([CH:18]=1)[C:10](=[O:12])[C:9]1[C:8](=[CH:7][CH:6]=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:13]=1)[N:14]=2)#[N:23]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 8189TriglymeHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 127191892-Amino-5-(propan-2-yloxy)benzoic acid

Product 1

HCID 130522978-cyano-2-isopropoxy-11-oxo-11H-pyrido[2,1-b]quinazoline

Procedure

A mixture of 16.7 g. of 5-isopropoxyanthranilic acid, 10.0 g. of 2-chloro-5-cyanopyridine and 0.01 g. of potassium iodide in 30 ml. of triglyme was heated to a bath temperature of 150° overnight under a stream of argon. On cooling, the mixture was triturated with ethanol and water. A gummy solid was collected, dissolved in hot ethyl acetate, filtered and the filtrate was evaporated to give 8.4 g. of crude product (38% yield). Two recrystallizations of this solid from dimethylformamide-acetic acid-water give pure 8-cyano-2-isopropoxy-11-oxo-11H-pyrido[2,1-b]quinazoline, mp 234°-236°.

Workup

  1. additionA mixture of 16.7 g
  2. temperatureOn cooling
  3. customthe mixture was triturated with ethanol and water
  4. customA gummy solid was collected
  5. dissolutiondissolved in hot ethyl acetate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customto give 8.4 g
  9. customTwo recrystallizations of this solid from dimethylformamide-acetic acid-water

Sources & evidence

ORD record
ord-56c68da9103c4ae9ba6ac005451764d0
Source dataset
uspto-grants-1982_09
Patent number
US04348396

Reaction notes

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